Cis-10-tetradecenyl acetate, an attractant component in the sex pheromone of the oak leaf roller moth (Archips semiferanus Walker)

The use of polymer supports in organic synthesis. VIII. Solid phase syntheses of insect sex attractants

“…similarly, hydrogenation and acetylation of 22 gave Poly~ner-bound Trityl Etlzer Alkenes 42, 43, and 45 7-dodecen-1-01 acetate (18) (28) portions of THF, one 20 ml portion of ethanol, four Sinlilarly, 23 yieldeil 9-tetradecen-1-ol acetate (19,26) 20 ml portions of water, two 20 ml portions of ethanol, (29) in high yield (Table 1). two 20 ml portions of dioxane, and three 20 ml portions ,-ompounds 28-30 were analyzed by and hplc of ether, and air dried to give polymer-bound alkene 42, to determine the amount of product in the supwhich did not exhibit a carbony1 absorption in its inposedly pure cis cornpounds and the data are recorded in frared spectrum.…”

Evidence for Origin of Insect Sex Pheromones: Presence in Food Plants

“…A series of 21 isomeric tetradecenyl acetates (6,7) were identified in the active sexual attractant fraction of the adult female; all isomers were active when tested on male OLR antennae by the electroantennogram (EAG) method (8). Seventeen of the 21 isomers proved attractive to OLR males when tested in field traps (8,9).…”

“…Because of similarities in the mass spectra and GC retention times of tetradecenyl acetate isomers having double bonds in the positions 2 through 8, further analyses of this component are being conducted. This isomer is one of the five most highly attractive isomers in field tests (8,9) in laboratory bioassays and field trials.…”